Reviewing the polyolefin cyclization reaction of the C35 polyprene catalyzed by squalene-hopene cyclase

Chemistry - A European Journal

Volumn 15, Issue 9, 2009, Pages 2091-2100

  Hoshino, Tsutomu ^a   Kumai, Yuko ^a   Sato, Tsutomu ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

Alkenes; Cyclization; Enzyme catalysis; Polycycles; Terpenoids

Indexed keywords

BOATS; CATALYSIS; DRUG PRODUCTS; ENZYMES; OLEFINS; POLYMERS;

ALKENES; CARBON FRAMEWORKS; CONVERSION RATIOS; CYCLIZATION PRODUCTS; CYCLIZATION REACTIONS; ENZYME CATALYSIS; POLYCYCLES; POLYCYCLIZATION; SINGLE PRODUCTS; SQUALENE-HOPENE CYCLASE; TERPENOIDS; TETRACYCLE; TETRACYCLIC PRODUCTS;

CYCLIZATION;

ALKENE; MUTASE; SQUALENE HOPENE CYCLASE; SQUALENE-HOPENE CYCLASE; TRITERPENE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; METABOLISM; REVIEW; STEREOISOMERISM;

ALKENES; CATALYSIS; CYCLIZATION; INTRAMOLECULAR TRANSFERASES; MOLECULAR STRUCTURE; STEREOISOMERISM; TRITERPENES;

EID: 60749124172     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802142     Document Type: Review

References (37)

1. Reviews: a) T. Hoshino, T. Sato, Chem. Commun. 2002, 291-301;
2. b) R. A. Yoder, J. N. Johnston, Chem. Rev. 2005, 105, 4730-4756;
3. c) K. U. Wendt, G. E. Schultz, E. J. Corey, D. R. Liu, Angew. Chem. 2000, 112, 2930-2952;
4. Angew. Chem. Int. Ed. 2000, 39, 2812-2833;
5. d) M. J. R. Segura, B. E. Jackson, S. P. T. Matsuda, Nat. Prod. Rep. 2003, 20, 304-317;
6. e) I. Abe. Nat. Prod. Rep. 2007, 24, 1311-1331.
7. T. Hoshino, S. Nakano, T. Kondo, T. Sato. A. Miyoshi, Org. Biomol. Chem. 2004, 2, 1456-1470.
8. Our studies: a) T. Sato, Y. Kanai, T. Hoshino. Biosci. Biotechnol. Biochem. 1998, 62, 407-411;
9. b) T. Sato, T. Abe, T. Hoshino. Chem. Commun. 1998, 2617-2618;
10. c) T. Sato, T. Hoshino, Biosci. Biotechnol. Biochem. 1999, 63, 1171-1180;
11. d) T. Hoshino, T. Sato, Chem. Commun. 1999, 2005-2006;
12. e) T. Hoshino, M. Kouda, T. Abe, S. Ohashi, Biosci. Biotechnol. Biochem. 1999, 63, 2038-2041;
13. f) T. Sato, T. Hoshino, Biosci. Biotechnol. Biochem. 1999, 63, 2189-2198;
14. g) T. Hoshino, T. Abe, M. Kouda., Chem. Commun. 2000, 441-442;
15. h) T. Hoshino, M. Kouda, T. Abe, T. Sato, Chem. Commun. 2000, 1485-1486;
16. i) T. Sato T. Hoshino. Biosci Biotechnol. Biochem. 2001, 65, 2233-2242;
17. j) T. Sato, S. Sasahara, T. Yamakami, T. Hoshino, Biosci. Biotechnol. Biochem. 2002, 66, 1660-1670;
18. k) T. Sato, M. Kouda, T. Hoshino, Biosci. Biotechnol. Biochem. 2004, 68, 728-738.
19. a) K. U. Wendt, K. Poralla, G.E. Schulz, Science 1997, 277, 1811-1815;
20. b) K. U. Wendt, A. Lenhart, G. E. Schulz, J. Mol. Biol. 1999, 286, 175-187;
21. c) D.J. Reinert, G. Balliano, G. E. Schulz, Chem. Biol. 2004, 11, 121-126.
22. N. Morikubo, Y. Fukuda, K. Ohtake, N. Shinya, D. Kiga, K. Sakamoto, M. Asanuma, H. Hirota, S. Yokoyama, T. Hoshino, J. Am. Chem. Soc. 2006, 128, 13184-13194.
23. T. Abe, T. Hoshino, Org. Biomol. Chem. 2005, 3, 3127-3139.
24. T. Hoshino, K. Shimizu, T. Sato, Angew. Chem. 2004, 116, 6868-6871;
25. Angew. Chem. Int. Ed. 2004, 43, 6700-6703.
26. a) M. Rohmer, P. Bouvier and G. Ourisson, Proc. Natl. Acad. Sci. USA 1979, 76, 847-851;
27. b) G. Ourisson, M. Rohmer and K. Poralla, Annu. Rev. Microbiol. 1987, 41, 301-333;
28. c) G. Ourisson, Pure Appl. Chem. 1989, 61, 345-348.
29. Our studies: a) T. Hoshino, T. Kondo, Chem. Commun. 1999, 731-732;
30. b) T. Hoshino, S. Ohashi, Org. Lett. 2002, 4, 2553-2556;
31. c) S. Nakano, S. Ohashi, T. Hoshino, Org. Biomol. Chem. 2004, 2, 2012-2022;
32. d) T. Hoshino, Y. Kumai, I. Kudo, S. Nakano, S. Ohashi, Org. Biomol. Chem. 2004, 2, 2650-2657;
33. e) T. Hoshino, Y. Yonemura, T. Abe, Y. Sugino. Org. Biomol. Chem. 2007, 5, 792-801.
34. a) H. Tanaka. H. Noguchi. I. Abe, Org. Lett. 2005, 7, 5873-5876;
35. b) H. Tanaka, H. Noma, H. Noguchi, I. Abe, Tetrahedron Lett. 2006, 47, 3085-3089.
36. I. Abe, H. Tanaka, H. Noguchi, J. Am. Chem. Soc. 2002, 124, 14514-14515.
37. I. Abe, M. Rohmer, J. Chem. Soc. Perkin Trans. 1 1994, 783-791.